dimethyl[(5-{[(2-{[(E)-1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}furan-2-yl)methyl]amine

• ChemBase ID: 741
• Molecular Formular: C13H22N4O3S
• Molecular Mass: 314.40378
• Monoisotopic Mass: 314.14126158
• SMILES: S(Cc1oc(CN(C)C)cc1)CCN/C(=C/[N+](=O)[O-])/NC
• Canonical SMILES: CN/C(=C\[N+](=O)[O-])/NCCSCc1ccc(o1)CN(C)C
• InChI: InChI=1S/C13H22N4O3S/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3/h4-5,9,14-15H,6-8,10H2,1-3H3/b13-9+
• InChIKey: VMXUWOKSQNHOCA-UKTHLTGXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dimethyl[(5-{[(2-{[(E)-1-(methylamino)-2-nitroethenyl]amino}ethyl)sulfanyl]methyl}furan-2-yl)methyl]amine
• IUPAC Traditional name: ranitidine.hcl
• Brand Name: Alquen; Alter-H2; Alvidina; Apo-Ranitidin; Artomil; Azuranit; Coralen; Digestosan; Ergan; Esofex; Fendibina; Gastrial; Gastridina; Gastrolav; Gastrosedol; Kuracid; Label; Lake; Logat; Melfax; Microtid; Mideran; Neugal; Noctone; Noktome; Normon; Novo-Radinine; Nu-Ranit; Pep-Rani; Ptinolin; Quadrin; Quantor; RAN; Radin; Ran H2; Ran Lich; Rani 2; Rani AbZ; Rani-BASF; Rani-Puren; Rani-Q; Rani-Sanorania; Rani-nerton; Raniben; Raniberl; Raniberta; Ranibloc; Ranic; Ranicux; Ranidil; Ranidin; Ranidine; Ranidura; Ranifur; Ranigasan; Ranigast; Ranigen; Ranilonga; Ranimerck; Raniogas; Raniplex; Ranisan; Ranitab; Ranitic; Ranitidin; Ranitidin 1A Pharma; Ranitidin AL; Ranitidin AWD; Ranitidin Arcana; Ranitidin Atid; Ranitidin Basics; Ranitidin Duncan; Ranitidin Dyna; Ranitidin Helvepharm; Ranitidin Heumann; Ranitidin Hexal; Ranitidin Merck; Ranitidin Millet; Ranitidin NM; Ranitidin Normon; Ranitidin PB; Ranitidin Stada; Ranitidin von ct; Ranitidin-Cophar; Ranitidin-Isis; Ranitidin-ratiopharm; Ranitidina Tamarang; Ranitidina predilu Grif; Ranitiget; Ranitin; Ranitine; Ranobel; Rantacid; Ranuber; Raticina; Regalil; Renatac; Rozon; Rubiulcer; Santanol; Serviradine; Sostril; Tanidina; Taural; Terposen; Toriol; Trigger; Ulcecur; Ulcex; Ulcirex; Ulcodin; Ulcolind Rani; Ulsaven; Ultidine; Viserul; Zandid; Zantac; Zantac 150; Zantac 75; Zantac In Plastic Container; Zantarac; Zantic
• Synonyms: Ranitidine hydrochloride; Ranitidine HCL; Ranitidine Base; Rantidine HCL; Ranitidine

Database IDs

• CAS Number: 66357-35-5
• PubChem SID: 160964204; 46505543
• PubChem CID: 3001055; 657345
• ATC CODE: A02BA07; A02BA02
• CHEMBL: 1790041
• Chemspider ID: 571454
• DrugBank ID: DB00863
• IUPHAR ligand ID: 1234
• KEGG ID: D00422
• Unique Ingredient Identifier: 884KT10YB7
• Wikipedia Title: Ranitidine
• Medline Plus: a601106

CALCULATED PROPERTIES

JChem

• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.5527394
• LogD (pH = 7.4): 0.21904218
• Log P: 0.98147845
• Molar Refractivity: 95.153 cm^3
• Polarizability: 32.323387 Å^3
• Polar Surface Area: 86.26 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.79
• LOG S: -3.6
• Solubility (Water): 7.95e-02 g/l

PROPERTIES

Physical Property

• Solubility: 24.7 mg/mL
• Hydrophobicity(logP): 1.3

Pharmacology Properties

• Admin Routes: Oral, IV
• Bioavailability: 39 to 88%
• Excretion: 30–70% Renal
• Half Life: 2–3 hours
• Metabolism: Hepatic
• Protein Bound: 15%
• Legal Status: OTC (US); P/POM (UK); S2 (Australia)
• Pregnancy Category: B (US); B1 (Australia)
• US Licence: Ranitidine

DETAILS

DrugBank - DB00863

• Drug Groups: approved
• Description: A non-imidazole blocker of those histamine receptors that mediate gastric secretion (H2 receptors). It is used to treat gastrointestinal ulcers. [PubChem]
• Indication: Used in the treatment of peptic ulcer disease (PUD), dyspepsia, stress ulcer prophylaxis, and gastroesophageal reflux disease (GERD).
• Pharmacology: Ranitidine is a histamine H2-receptor antagonist similar to cimetidine and famotidine. An H2-receptor antagonist, often shortened to H2 antagonist, is a drug used to block the action of histamine on parietal cells in the stomach, decreasing acid production by these cells. These drugs are used in the treatment of dyspepsia, however their use has waned since the advent of the more effective proton pump inhibitors. Like the H1-antihistamines, the H2 antagonists are inverse agonists rather than true receptor antagonists.
• Toxicity: LD₅₀=77mg/kg (orally in mice). Symptoms of overdose include muscular tremors, vomiting, and rapid respiration.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Ranitidine is metabolized to the N-oxide, S-oxide, and N-desmethyl metabolites, accounting for approximately 4%, 1%, and 1% of the dose, respectively.
• Absorption: Approximately 50% bioavailability orally.
• Half Life: 2.8-3.1 hours
• Protein Binding: 15%
• Elimination: The principal route of excretion is the urine (active tubular excretion, renal clearance 410mL/min), with approximately 30% of the orally administered dose collected in the urine as unchanged drug in 24 hours.
• Distribution: * 1.4 L/kg; * 1.76 L/kg [clinically significant renal function impairment (creatinine clearance 25 to 35 mL/min)]
• Clearance: * 29 mL/min [clinically significant renal function impairment]; * 3 mL/min/Kg [neonatal patients]
• External Links: Wikipedia; RxList; Drugs.com